Aluminium lithium hydride → 1-(2'-Fluoro-4-hydroxymethyl-5'-methoxy-biphenyl-2-yl)-2,2-dimethyl-but-3-en-1-ol

HRID 404383Notes

Reaction equation

HRID 404383 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:12]=2[F:19])=[C:7]([CH:20]([OH:26])[C:21]([CH3:25])([CH3:24])[CH:22]=[CH2:23])[CH:6]=1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[F:19][C:12]1[CH:13]=[CH:14][C:15]([O:17][CH3:18])=[CH:16][C:11]=1[C:8]1[CH:9]=[CH:10][C:5]([CH2:3][OH:2])=[CH:6][C:7]=1[CH:20]([OH:26])[C:21]([CH3:25])([CH3:24])[CH:22]=[CH2:23]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 574676322'-Fluoro-2-(1-hydroxy-2,2-dimethyl-but-3-enyl)-5'-methoxy-biphenyl-4-carboxylic acid methyl ester

Product 1

HCID 574676511-(2'-Fluoro-4-hydroxymethyl-5'-methoxy-biphenyl-2-yl)-2,2-dimethyl-but-3-en-1-olYield 90.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 21.4 (530 mg, 1479 μmol) in THF (20 mL), was added LAH (168 mg, 4436 μmol). The resulting mixture was stirred at room temperature for 1 hour. The solvent was then removed, and the residue was diluted with EtOAc. The organic layer was washed with 1N NaOH, water, and brine. The organic layer was then dried over sodium sulfate, filtered, and the organic solvent was removed in vacuo to give an oil (442 mg, 90%) which was used without further purification. MS ESI m/e: 331.2 (M+H)+.

Workup

  1. customThe solvent was then removed
  2. additionthe residue was diluted with EtOAc
  3. washThe organic layer was washed with 1N NaOH, water, and brine
  4. dry with materialThe organic layer was then dried over sodium sulfate
  5. filtrationfiltered
  6. customthe organic solvent was removed in vacuo

Sources & evidence

ORD record
ord-f668ddaed1f64da0b91c7570f2dc6eab
Source dataset
uspto-grants-2014_06
Patent number
US08748462B2

Reaction notes

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